(2-苯并噻唑基硫代)-乙腈 | 24793-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: (2-苯并噻唑基硫代)-乙腈
• 英文名称: (benzothiazolyl-2-thio)acetonitrile
• 英文别名: (2-benzothiazolylthio)acetonitrile；1-(benzothiazol-2-yl-thio)acetonitrile；2-(benzo[d]thiazol-2-ylthio)acetonitrile；(1,3-benzothiazol-2-ylsulfanyl)acetonitrile；benzothiazol-2-ylsulfanyl-acetonitrile；2-(benzothiazol-2-ylthio)acetonitrile；2-Cyanomethylthiobenzothiazole；2-(1,3-Benzothiazol-2-ylsulfanyl)acetonitrile
• CAS: 24793-01-9
• 化学式: C₉H₆N₂S₂
• mdl: MFCD00104617
• 分子量: 206.292
• InChiKey: GWSJKSFGUSSSKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-苯并噻唑基硫代)-乙腈 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以77%的产率得到2-benzothiazolyl cyanomethyl sulfoxide
  参考文献：
  名称：

  Formation of Thioaldehyde Intermediates by Thermolysis of Sulfoxides Bearing Some Heteroaromatics

  摘要：

  Thermal reactions of phenacyl sulfoxide bearing heterocycles, such as a 2-benzothiazolyl or N-oxypyridyl group, in the presence of 2,3-dimethyl-1,3-butadiene afforded 6-benzoyl-5,6-dihydro-3,4-dimethyl-2H-thiapyran in good yield. This product is considered to be formed by the Diels-Alder reaction of a diene with thioaldehyde formed initially by the decomposition of sulfoxides.

  DOI：

  10.1021/jo9700181
• 作为产物：
  描述：

  2-巯基苯并噻唑 以 四氢呋喃 、 苯 为溶剂， 生成 (2-苯并噻唑基硫代)-乙腈
  参考文献：
  名称：

  Thio and sulfonyl glyoxylnitrileoxime phosphates and phosphonates

  摘要：

  式##EQU1##中的化合物，其中R是低碳烷基；R.sub.1是低碳烷基或低碳烷氧基；X是硫或磺酰基；R.sub.2是烷基，苯并噻唑，苄基，萘基，苯并二唑-1,3，噻唑，苯基或取代苯基，其中所述取代基是氯，溴，甲基或甲氧基，并且这些化合物作为杀虫剂的用途。

  公开号：

  US03931358A1
• 作为试剂：
  描述：

  糠醛 、 5,5-二甲基-1,3-环己二酮 在 哌啶 、 (2-苯并噻唑基硫代)-乙腈 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以81%的产率得到2-[furan-2-yl-(6'-hydroxy-4',4'-dimethyl-2'-oxocyclohex-6'-enyl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone
  参考文献：
  名称：

  New route for synthesis, spectroscopy, and X-ray studies of 2-[aryl-(6′-hydroxy-4′,4′-dimethyl-2′-oxocyclohex-6′-enyl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone and 1,8-dioxo-octahydroxanthenes and antitumor evaluation

  摘要：

  Treatment of 1-(benzothiazol-2-yl-thio)-acetonitrile 1 with 5,5-dimethyl-1,3-cyclohexanedione-(dimedone) 2 and aromatic aldehyde 3a, b in refluxing ethanol containing a catalytic amount of piperidine lead to bisdimedone derivatives 5a and b in short periods of times with excellent yields and not 4H-chromen-5(6H)-one derivatives 8. The compound 5a was then cyclized to 1,8-dioxo-octahydroxanthene derivative 6. The structures of the synthesized compounds were elucidated by elemental analysis H-1 NMR and C-13 NMR spectra, COSY, HSQC, HMBC, MS, and X-ray crystallographic investigations. The cytotoxicity of the synthesized compounds 5a, b, and 6 were studied and evaluated. Three human tumor and three normal cell lines, namely as breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268), human fibroblast (WI-38), normal prostate epithelial cells, and normal colon mucosal, NCM 460 cells, respectively. The tested compounds were found to exhibit higher inhibitory effects toward the tumor and normal cell lines than the reference drug, doxorubicin.

  DOI：

  10.1007/s00044-013-0712-3

文献信息

• Novel substituted benzothiazole and Imidazo[2,1-b][1,3,4]Thiadiazole derivatives: Synthesis, characterization, molecular docking study, and investigation of their in vitro antileishmanial and antibacterial activities
  作者：Mustafa Er、Arif Özer、Şahin Direkel、Tuncay Karakurt、Hakan Tahtaci

  DOI：10.1016/j.molstruc.2019.05.104

  日期：2019.10

  thiosemicarbazide in trifluoroacetic acid (TFA) (in yields of 83% and 84%). Finally, we synthesized the imidazo[2,1-b][1,3,4]thiadiazole derivatives (5-24) containing benzothiazole group, which are the target compounds, from reactions of 2-amino-1,3,4-thiadiazole derivatives (4a,b) with phenacyl bromide derivatives (in yields of 53%–73%). All of the compounds synthesized were characterized with 1H NMR, 13C NMR

  摘要 本研究合成了新型的含苯并噻唑基团的咪唑并[2,1-b][1,3,4]噻二唑衍生物。为此，我们首先以高产率（分别为 82% 和 87%）获得了原料苯并[d]噻唑-2-基硫基/氧基乙腈化合​​物（3a，b）。然后，我们通过这些腈衍生物 (3a,b) 与氨基硫脲在三氟乙酸 (TFA) 中的反应合成了 2-氨基-1, 3,4-噻二唑衍生物 (4a,b)（产率分别为 83% 和 84 %）。最后，我们从2-氨基-1,3,4-的反应中合成了目标化合物含有苯并噻唑基团的咪唑并[2,1-b][1,3,4]噻二唑衍生物(5-24)。噻二唑衍生物 (4a,b) 与苯甲酰溴衍生物（产率为 53%–73%）。合成的所有化合物均经 1H NMR、13C NMR、FT-IR、元素分析、和质谱。对研究中合成的化合物进行了抗利什曼原虫和抗菌活性测试。据观察，化合物 8 具有最高的抗利什曼原虫活性（MIC = 10 000
• Trisubstituted Highly Activated Benzo[<i>d</i>]thiazol-2-yl-sulfone-Containing Olefins as Building Blocks in Organic Synthesis
  作者：Ondřej Kováč、František Zálešák、David J.-Y. D. Bon、Lukas Roiser、Lubomír V. Baar、Mario Waser、Jiří Pospíšil

  DOI：10.1021/acs.joc.0c00571

  日期：2020.6.5

  molecular scaffolds. Synthesis of 1,1-deactivated olefins substituted with a BT-sulfonyl group and a carbonyl or nitrile, respectively, consists of unusual Ti(OPri)4-mediated Knoevenagel-type condensation and proceed in good to excellent yields. Generated olefins can be further transformed in a highly stereoselective manner and in good yields to various polyfunctionalized heterocycles and acyclic molecular

  在本文中，我们报告了高度亲电子的1,1-失活烯烃的形成，它们作为新型合成构件的使用以及它们向结构多样的分子支架的转化。分别被BT-磺酰基和羰基或腈取代的1,1-失活烯烃的合成由不寻常的Ti（OPr i）4组成介导的Knoevenagel型缩合反应，收率好至极好。产生的烯烃可以高度立体选择性的方式和高收率进一步转化为各种多官能化杂环和无环分子支架。总体而言，从（主要是）市售醛开始，分两到四个步骤获得所得结构。另外，在制备的结构中BT-磺酰基的存在允许进一步的化学选择性官能化/合成后转化以提供结构上多样化的最终化合物。
• Synthesis and E/Z Configuration Determination of Novel Derivatives of 3-Aryl-2-(benzothiazol-2'-ylthio) Acrylonitrile, 3-(Benzothiazol-2'-ylthio)-4-(furan-2''-yl)-3-buten-2-one and 2-(1-(Furan-2''-yl)-3'-oxobut-1''-en-2-ylthio)-3-phenylquinazolin-4(3H)-one
  作者：Fatima Al-Omran、Rafat M. Mohareb、Adel Abou El-Khair

  DOI：10.3390/molecules16076129

  日期：——

  Knoevenagel condensation of 2-(benzothiazol-2-ylthio) acetonitrile (2) with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a–b exclusively, while the condensation of the compound 2 with benzaldehyde or para-substituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c–e with preferentially formation of the E-isomer. Condensation of furan-2-carbaldehyde (3a) with either 1-(benzothiazol-2'-ylthio) propan-2-one (5) or 2-(2'-oxo propylthio)-3-phenyl-quinazolin-4(3H)-one (9) leads exclusively to the Z-isomers of 6 and 10, respectively. The structures of the newly synthesized compounds were elucidated by elemental analyses, 1H-NMR and 13C-NMR spectra, COSY, HSQC, HMBC, NOE, MS and X-ray crystallographic investigations.

  2-(苯并噻唑-2-基硫)乙腈（2）与呋喃-2-醛或噻吩-2-醛的Knoevenagel缩合反应独家生成E异构体4a–b，而化合物2与苯甲醛或带有施电子基团的对位取代苯甲醛的缩合反应则得到E/Z混合物4c–e，E异构体优先生成。呋喃-2-醛（3a）与1-(苯并噻唑-2'-基硫)丙-2-酮（5）或2-(2'-氧基丙基硫)-3-苯基喹唑啉-4(3H)-酮（9）的缩合反应则独家生成Z异构体6和10，分别。新合成化合物的结构通过元素分析、1H-NMR和13C-NMR谱、COSY、HSQC、HMBC、NOE、MS以及X射线晶体学研究得以阐明。
• Synthesis and Anti-Proliferative Activity of New Acridinyl and Benzothiazolyl-Based Triazole Glycosides via Click Cycloaddition and Their Tetrazolyl Analogs
  作者：Hala E. M. Tolan、Mohamed A. A. Radwan、Hanan A. Soliman、Hanem M. Awad、Wael A. El-Sayed

  DOI：10.1134/s1068162020060345

  日期：2020.11

  and the triazole ring or between the benzothiazole and the triazole rings as isosteric analogs of the synthesized glycosyl triazoles were also prepared by click cycloaddition. Furthermore, new tetrazolyl glycosides attached to the benzothiazole ring system as analogs of triazole glycosides were synthesized. The desired products were examined against different tumor cells such as the human colon (HCT-116)

  摘要 利用Cu(I)-催化的叠氮-炔环加成(CAAC)点击反应合成了新型吖啶和苯并噻唑取代的1,2,3-三唑苷。在点击反应条件下，起始取代的炔衍生物与吡喃糖基叠氮化物的反应得到相应的 1,2,3-三唑乙酰化 N-糖苷产物。此外，还通过点击环加成制备了在糖部分与三唑环之间或苯并噻唑与三唑环之间具有连接间隔基的 1,2,3-三唑糖苷，作为合成的糖基三唑的等排类似物。此外，合成了新的四唑基糖苷作为三唑糖苷的类似物连接到苯并噻唑环系统。使用 MTT 测定法针对不同的肿瘤细胞，例如人结肠 (HCT-116)、人肺癌 (A549)、肝细胞癌 (HepG2) 和乳腺癌 (MCF-7) 癌细胞系对所需产物进行了检测。通常，大多数所需化合物对所有肿瘤细胞都显示出优异的活性。结果还表明，高活性化合物是基于苯并噻唑基的三唑糖苷。
• Heterocyclic substituted thio and sulfonyl glyoxylinitrileoxime
  申请人：Stauffer Chemical Company

  公开号：US04006154A1

  公开（公告）日：1977-02-01

  Compounds of the formula ##STR1## in which R is lower alkyl; R.sub.1 is lower alkyl or lower alkoxy; X is thio or sulfonyl; R.sub.2 is alkyl, benzothiazol-2-yl, benzyl, naphthyl, benzimidazol-2-yl, thiazol-2-yl, phenyl or substituted phenyl wherein said substituents are chloro, bromo, methyl or methoxy and the use of these compounds as insecticides.

  化合物的公式为##STR1##其中R为较低的烷基；R.sub.1为较低的烷基或较低的烷氧基；X为硫醇或磺酰基；R.sub.2为烷基，苯并噻唑-2-基，苄基，萘基，苯并咪唑-2-基，噻唑-2-基，苯基或取代苯基，其中所述取代基为氯，溴，甲基或甲氧基，以及这些化合物作为杀虫剂的用途。